Charles Darrow, after having trouble getting Parker Brothers to buy his game, hired an unknown artist to help with a redesign after the original 1935 release became a blockbuster success. The character first appeared on Chance and Community Chest cards in the 1936 version of Monopoly and has appeared on every version released since. The artist who designed the iconic character remains unidentified, not unlike Pennybags himself, who is universally recognized yet nameless to most people. Possible explanations attributing the work to Albert Richardson, Parker Brothers' first traveling salesman, who used a similar character design on his business cards, or sighting the "Little Esky" mascot used by Esquire magazine as a potential model have not been verified. Because of his largely anonymous existence as a corporate trademark, Rich Uncle Pennybags didn't even receive a first name until 1988, when the "Monopoly Companion" dubbed him Milburn. In 2000, with Parker Brothers now a wholly owned subsidiary of toy giant Hasbro, Rich Uncle Pennybags was renamed "Mr. Monopoly", a move not entirely welcomed by fans.

How rich is your Uncle?

If a regular round of Monopoly is any indicator, Pennybags is a Wall Street washout. The financial impact of many of the events listed on Community Chest and Chance cards show Pennybags to be a live by the seat of your pants financier, subject to bouts of bad luck that see him often cooling his heels in jail. Was he the Donald Trump of his day, all flash and no cash? It would seem so. The great success of Monopoly during the 1930s likely has a great deal to do with people enjoying the trials and tribulations of a top-hatted socialite hoisted by his trousers and tossed in the clink. Should we feel bad for Pennybags, trapped in his karmic wheel of winfall and downfall? Hard to say, but he seems to be enjoying himself.

Your Uncle gets around

Being the star mascot of the most successful American board game ever produced isn't enough work for Pennybags. His image has been used continuously since his introduction in 1936. Pennybags was first used outside of Monopoly in the Parker Brothers' 1940 game "Dig", and then again in 1946, starring in a game appropriately dubbed "Rich Uncle". 1985 saw him used in "Advance to Boardwalk", and in 1988 "Free Parking" used his image as well. As the official Monopoly figurehead, his use in 1990s "Monopoly Junior" was not a big surprise. Hasbro has been licensing Monopoly special editions, using different brands, like NFL teams or cartoon characters (yes, Pokémon Monopoly). In each of these versions, Rich Uncle Pennybags is still used. No version of Monopoly has ever been released without featuring Pennybags in some way.